Fluorine atom-containing polycondensable silicon compounds are useful as a raw material for materials having characteristics such as weather resistance, heat resistance, chemical resistance, low refraction properties, water and oil repellency, water droplet sliding properties, lubricity, release properties, etc., and for example, compounds represented by CF3(CF2)nCH2CH2SiX3 (wherein n represents an integer of from about 3 to 10; and X represents a chlorine atom, an alkoxy group, an isocyanate group, etc.) are known. Though polymer materials, film materials, coating agents and the like obtained from these raw materials exhibit high water repellency, they were not satisfactory from the viewpoints of strength and scratching properties because only one condensable silicon group is present in one molecule. Also, there was involved a problem in water droplet sliding properties.
From the viewpoint of enhancing the scratch resistance, there is known an example utilizing a fluorine-containing compound having two trialkoxysilyl groups in one molecule, represented by (RO)3SiCH2CH2(CF2)nCH2CH2Si(OR)3 (see Patent Document 1). However, though such a compound is, for example, obtained by allowing a fluorine-containing diene compound represented by CH2═CH(CF2)nCH═CH2, trichlorosilane and a Pt catalyst to react in a sealed tube at 100° C. for 50 hours, followed by treating with sodium methoxide (see Non-Patent Document 1), it is difficult to economically produce the compound on an industrial scale. Also, the raw material fluorine-containing diene is problematic in production aptitude and availability.
Also, from the viewpoint of enhancing the water droplet sliding properties, there is known an example utilizing a compound such as CH3(CF2)nCH2CH2Si (OR), etc. (see Patent Document 2). However, with respect to such a compound, a reaction between a fluorine-containing olefin compound represented by CH3(CF2)nCH═CH2 and trichlorosilane is necessary, and there were involved problems in production aptitude and availability of the fluorine-containing olefin.
As a method for simply and easily producing a fluorine atom-containing polycondensable silicon compound, there is known an example in which a fluorine-containing alcohol, CF3(CF2)nCH2OH and an isocyanate group-containing polycondensable silicon compound are allowed to react in the presence of an Sn catalyst to obtain a carbamic acid ester in a high yield (see Patent Document 3). However, an example for applying to a polyfunctional alcohol has not been known yet. Also, the Sn catalyst is not preferable from the environmental standpoint.
Patent Document 1: WO 05/059051
Patent Document 2: JP-A-11-116943
Patent Document 3: WO 05/121156
Non-Patent Document 1: Journal of Oleo Science, 51(5), pages 305 to 311 (2002)